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The couple recently reunited and Mr. Sheppard was supposed to move back in that day, she said. But after dozing intermittently, Mr. Sheppard insisted on bicycling back to his own apartment.

Details that suggest cyclist had been drinking may help former AG muster a solid legal defence - but is there room for a moral one?

Leaving Ms. Bailey's, he was immediately apprehended by Toronto police, who were responding to a call of "unknown trouble" at the building. Mr. Sheppard was placed into the back of the police cruiser.

For Ms. Bailey, this is where she last saw her boyfriend alive. It is also where she wishes he could have stayed, and that the police could have driven him all the way home in one piece.

"I asked for the police to give him a ride home," said Ms. Bailey, 34, adding that her friends also made similar requests. "They said 'No, he's going to [take]himself home."

Shortly afterward, Mr. Sheppard was killed in a collision with a black Saab convertible on Bloor Street West, just east of Avenue Road. Former attorney-general Michael Bryant has been charged in connection with the death.

Police are now investigating the circumstances around the incident, including witness reports that Mr. Sheppard may have grabbed onto the car wheel. Police are also reviewing security camera footage from stores along the retail strip, some of which captured parts of the altercation.

Police also say they knew Mr. Sheppard had been drinking that night, but ultimately decided he was fit to get home on his own.

"At the time, I believe a good decision was made," said Staff Sergeant John Spanton with 51 Division. "In terms of his sobriety, the officers made the decision that he was okay. And I would stand behind that."

Meanwhile, a vigil for Mr. Sheppard was held late Wednesday afternoon, filling almost a block of Bloor Street with more than 200 bicycles. Bells chimed as a swarm of bike couriers, cycling advocates and mourners coasted east along Bloor Street West.

They laid their bicycles on the road, reducing one block of Bloor Street West to a single lane. After five minutes of silence, they raised their bicycles in the air and shouted or barked, a rallying cry for couriers and cyclist safety.

A memorial also grew at the Bloor Street sidewalk where Mr. Sheppard lay in a bloodied heap. Flowers were taped to a tree he reportedly struck and a grey mailbox was also covered in messages scrawled on yellow sticky notes.

Ms. Bailey contributed pink flowers and a small wooden carving of a dragon and turtle, symbolic of their relationship, she said.

Her blue eyes welled with tears as she remembered her "fun-loving" and "vibrant" comedian boyfriend. The couple have been dating since Christmas but first met 15 years ago in their hometown Edmonton.

Mr. Sheppard, a 33-year-old father of four, reportedly moved to Toronto about eight years ago, leaving behind a checkered past which included allegations of cheque forgery and 61 criminal charges.

Jodie Schlender, the mother of one of his children, told the Canadian Press that Mr. Sheppard also struggled with alcohol problems.

She said she always thought her ex-partner might die on the harried streets of downtown Toronto.

"He's going to be really missed," Ms. Schlender said from Hinton, Alta., her voice faltering with emotion.